Water → 4-[3-(3,5-Difluorophenyl)prop-2-ynylidene]piperidine

HRID 1895983Notes

Reaction equation

HRID 1895983 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH:11]=[C:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH:5]=[C:6]([F:8])[CH:7]=1.FC(F)(F)C(O)=O.O.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH:11]=[C:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86627341tert-Butyl 4-[3-(3,5-difluorophenyl)prop-2-ynylidene]piperidine-1-carboxylate

Product 1

HCID 866273424-[3-(3,5-Difluorophenyl)prop-2-ynylidene]piperidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of Compound 228a (0.090 g, 0.27 mmol) in CHCl3 (1 mL) was added trifluoroacetic acid (0.42 mL, 5.4 mmol) and the reaction mixture was then stirred at 70° C. for 15 min. until the complete conversion of the reagent was observed by LC-MS. After cooling to r.t., water was added and the solution was alkalinized by addition of 2 N NaOH. The solution was extracted with CH2Cl2, the organic layer washed with brine and dried over Na2SO4 affording the title compound (0.051 g).

Workup

  1. temperatureAfter cooling to r.t.
  2. extractionThe solution was extracted with CH2Cl2
  3. washthe organic layer washed with brine
  4. dry with materialdried over Na2SO4 affording the title compound (0.051 g)

Sources & evidence

ORD record
ord-8b589b94c28649c7b37fc27d949fd9f1
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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